When Angelina Jolie and The Weeknd were seen together in public back in 2021, the world couldn’t stop buzzing. It wasn’t just the fact that these two were spotted out—it was who they were: an Oscar-winning actress and humanitarian, and one of the biggest names in music, dining together under the stars in Los Angeles. Was it a budding romance? A Hollywood power collaboration? Or just two famous people with shared interests?
Let’s rewind to that night in late September 2021. Jolie and The Weeknd (real name Abel Tesfaye) were spotted having dinner at Giorgio Baldi, an upscale Italian restaurant in Santa Monica.
It wasn’t their first visit either. They had dined at the same spot earlier that summer, sparking similar waves of speculation at the time. But this second dinner confirmed for many fans that something was definitely brewing.
Paparazzi snapped shots of the duo arriving separately but leaving within minutes of each other. They both wore black—Angelina in a chic black trench and The Weeknd in his signature street-style flair. The moment was intimate, classy, and, above all, intriguing. It felt like a scene from one of Jolie’s movies: quiet, calculated, and loaded with subtext.
Naturally, rumors flew. Social media lit up with questions. Were they dating? Were they working on a project together? Was this a casual meetup or the beginning of something serious?
Well, according to multiple sources who spoke with E! News, the answer isn’t as scandalous as some hoped. Despite the romantic optics, insiders insisted that the pair weren’t romantically involved—at least not at that time.
“They are not dating,” a source told the outlet plainly. “They have mutual interests and are enjoying putting their ideas together to see what they can come up with.”
Another insider explained that the two bonded over humanitarian interests and creative endeavors. “They have been recently talking about partnering on a few humanitarian projects together,” the source shared. “He loves talking about movies and the art form.”
The Weeknd, after all, isn’t just a chart-topping artist—he’s been slowly building his film and television resume, including a major deal with HBO. He’s also well-known for his philanthropy and activism, especially on issues related to racial justice and global humanitarian efforts.
Angelina Jolie, of course, has long been associated with global activism through her work with the UN and other organizations. On paper, they make a surprising but oddly fitting duo.
So, what was really going on between them?
Another source close to the pair noted that while the two had become close, there was no romance—at least not officially. “They’ve been enjoying each other’s company,” the insider said. “But they aren’t dating. He has been enjoying getting to know her and feels they’ve formed a close bond.”
According to the same report, Jolie and The Weeknd met through mutual connections in the entertainment world. “They have a lot in common,” the source said. “They totally hit it off after their first meeting earlier this summer and have kept in touch ever since.”
Still, fans weren’t entirely convinced by these denials. After all, both stars are notoriously private about their love lives. If something was happening behind closed doors, they were unlikely to confirm it—especially considering how much media scrutiny they’ve both endured in past relationships.
Angelina Jolie, for one, was still dealing with the fallout from her highly publicized divorce from Brad Pitt. The couple, who share six children together, had been entangled in a bitter and ongoing custody battle since their split in 2016. For Jolie, navigating any new relationship—especially one that could make headlines—was bound to be complicated.
Meanwhile, The Weeknd had his own history of headline-making romances. He had an on-again, off-again relationship with supermodel Bella Hadid that began in 2015 and lasted, with a few interruptions, until 2019.
In between those periods, he dated Selena Gomez, though that relationship ended after less than a year. In a 2021 interview with GQ, he acknowledged the complexities of dating in the public eye.
“I do feel guilty,” he said when asked about dating someone who isn’t famous. “That’s why I don’t…I try not to do too much. I just try not to bring attention to myself. And I just love being in normal situations, man. It’s such a great feeling. To be able to just like go on a walk and not be in a f–king SUV.”
His comments suggested a desire to avoid the media circus that can come with celebrity relationships. And in that sense, a low-key, unconfirmed connection with someone like Jolie—who’s equally private—might have suited him perfectly.
So, did Angelina Jolie and The Weeknd secretly date after her divorce? The honest answer is… we still don’t know for sure. If they did, they kept it extremely under wraps. But all public signs, and statements from sources close to them, suggest that while there was genuine chemistry and mutual admiration, it never crossed the line into romance—or at least not publicly.
It’s entirely possible their connection was purely creative. Jolie is known for collaborating with global thinkers, artists, and activists, and The Weeknd has been expanding his influence beyond music. In many ways, their dinners could have simply been the result of two influential minds brainstorming ideas over pasta and wine.
And yet, there’s always that nagging curiosity—especially when it comes to celebrity pairings that feel unexpected. Maybe it’s because they come from such different worlds. Maybe it’s because they both carry an air of mystery. Or maybe it’s just because, as fans, we love the idea of two enigmatic stars finding something special in each other.
Whatever the truth is, Angelina Jolie and The Weeknd’s brief, paparazzi-documented connection will likely remain one of those Hollywood what-ifs. Not quite a romance, not quite a fling—just two celebrities, sharing dinners, sharing ideas, and sparking rumors that, for a moment, had everyone talking.
And who knows? Maybe that’s all it was ever meant to be.
